LiHMDS tetrahydrofuran → HCID 69957539, compound

HRID 1937135Notes

Reaction equation

HRID 1937135 reaction equation
[O:1]1[C@H:9]2[C@@H:10]3[C@@H:14]([C@@H:2]1[C@H:3]1[C@@H:8]2[CH2:7][CH2:6][CH2:5][CH2:4]1)[C@@H:13]([CH3:15])[O:12][C:11]3=[O:16].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CCCC1>>[OH:1][C@@H:2]1[C@H:14]2[C:10]([C:11](=[O:16])[O:12][C@@H:13]2[CH3:15])=[CH:9][C@H:8]2[C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2

Participants

3

Reactant 2

HCID 23714775LiHMDS tetrahydrofuranHCID 69957560HCID 69957560, compound

Product 1

HCID 69957539HCID 69957539, compoundYield 101.5%

Procedure

Similarly to Example 3, 1.35 g(6.07 mmol) of (3R,3aR,4S,4aR,8aS,9R,9aS)-4,9-epoxy-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one were reacted with 27.6 mg(5 equivalents) of lithium bis(trimethylsilyl)amide-tetrahydrofuran solution(1.1M) to obtain 1.37 g of (3R,3aR,4S,4aR,8aS)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,8a-octahydronaphtho[2,3-c]furan-1(3H)-one and then reacted with 4.54 ml(5 equivalents) of 1,8-diazabicyclo[5.4.0]undec-7-ene to obtain 1.05 g of (3R,3aR,4S,4aR,9aR)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,9a-octahydronaphtho[2,3-c]furan-1(3H)-one(yield after 2 processes 78%).

Sources & evidence

ORD record
ord-943a651e55bf457b96a0dd158598fbdb
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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